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Hexamethylbenzene
Hexamethylbenzene, also known as mellitene, is a hydrocarbon with the molecular formula C12H18 and the condensed structural formula C6(CH3)6. It is an aromatic compound and a derivative of benzene, where benzene's six hydrogen atoms have each been replaced by a methyl group. In 1929 Kathleen Lonsdale reported the crystal structure of hexamethylbenzene, demonstrating that the central ring is hexagonal and flat and thereby ending an ongoing debate about the physical parameters of the benzene system. This was a historically significant result, both for the field of X-ray crystallography and for understanding aromaticity. The compound can be prepared by reacting phenol with methanol at elevated temperatures over a suitable solid catalyst such as alumina. The mechanism of the process has been studied extensively, with several intermediates having been identified. Alkyne trimerisation of dimethylacetylene also yields hexamethylbenzene in the presence of a suitable catalyst. Hexamet ...
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Benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a precursor to the manufacture of chemicals with more complex structure, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major industrial chemical, it finds limited use in consumer items because of its toxicity. History Discovery The word "''benzene''" derives from "''gum benzoin''" (benzoin res ...
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Organoruthenium Chemistry
Organoruthenium chemistry is the chemistry of organometallic compounds containing a carbon to ruthenium chemical bond. Several organoruthenium catalysts are of commercial interest and organoruthenium compounds have been considered for cancer therapy. The chemistry has some stoichiometric similarities with organoiron chemistry, as iron is directly above ruthenium in group 8 of the periodic table. The most important reagents for the introduction of ruthenium are ruthenium(III) chloride and triruthenium dodecacarbonyl. In its organometallic compounds, ruthenium is known to adopt oxidation states from -2 ( u(CO)4sup>2−) to +6 ( uN(Me)4sup>−). Most common are those in the 2+ oxidation state, as illustrated below. File:Grubbs Catalyst 1st Generation.svg, 1st generation Grubbs catalyst File:ShvoCat.png, Shvo catalyst File:RuCymCl2.png, (cymene)ruthenium dichloride dimer File:Trirutheniumdodecacarbonyl.svg, triruthenium dodecacarbonyl. File:Chloro(cyclopentadienyl)bis(triphenylp ...
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Acetic Acid
Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements. Acetic acid is the second simplest carboxylic acid (after formic acid). It is an important Reagent, chemical reagent and industrial chemical, used primarily in the production of cellulose acetate for photographic film, polyvinyl acetate for wood Adhesive, glue, and synthetic fibres and fabrics. In households, diluted acetic acid is often used in descaling agents. In the food industry, acetic acid is controlled by the E number, food additive code E260 as an acidity regulator and as a condiment. In biochemistry, the acetyl group, derived from acetic acid, is fundamental to all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats. The global ...
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Phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs. Properties Phenol is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.895 M). Homogeneous mixtures of phenol and water at phenol ...
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Organometallic Compound
Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide (metal carbonyls), cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganics, metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complex ...
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Ligand
In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electron pairs, often through Lewis bases. The nature of metal–ligand bonding can range from covalent to ionic. Furthermore, the metal–ligand bond order can range from one to three. Ligands are viewed as Lewis bases, although rare cases are known to involve Lewis acidic "ligands". Metals and metalloids are bound to ligands in almost all circumstances, although gaseous "naked" metal ions can be generated in a high vacuum. Ligands in a complex dictate the reactivity of the central atom, including ligand substitution rates, the reactivity of the ligands themselves, and redox. Ligand selection requires critical consideration in many practical areas, including bioinorganic and medicinal chemistry, homogeneous catalysis, and environmental chemi ...
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Mellite
Mellite, also called honeystone, is an unusual mineral being also an organic chemical. It is chemically identified as an aluminium salt of mellitic acid, and specifically as aluminium benzene hexacarboxylate hydrate, with the chemical formula Al2C6(COO)6·16H2O.http://webmineral.com/data/Mellite.shtml Webmineral data It is a translucent honey-coloured crystal which can be polished and faceted to form striking gemstones. It crystallizes in the tetragonal system and occurs both in good crystals and as formless masses. It is soft with a Mohs hardness of 2 to 2.5 and has a low specific gravity of 1.6.http://rruff.geo.arizona.edu/doclib/hom/mellite.pdf Handbook of Mineralogy It was discovered originally in 1789 at Artern in Thuringia, Germany. It has subsequently also been found in Russia, Austria, the Czech Republic, and Hungary. It was named from the Greek ''meli'' "honey", in allusion to its color. It is found associated with lignite and is assumed to be formed from plant materia ...
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Salt (chemistry)
In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively charged sodium ions and negatively charged chloride ions. The component ions in a salt compound can be either inorganic, such as chloride (Cl−), or organic, such as acetate (). Each ion can be either monatomic, such as fluoride (F−), or polyatomic, such as sulfate (). Types of salt Salts can be classified in a variety of ways. Salts that produce hydroxide ions when dissolved in water are called ''alkali salts'' and salts that produce hydrogen ions when dissolved in water are called ''acid salts''. ''Neutral salts'' are those salts that are neither acidic nor basic. Zwitterions contain an anionic and a cationic centre in the same molecule, but are not considered salts. Examples of zwitterions are amino acids, many metabolites, peptid ...
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Mellitic Acid
Mellitic acid, also called graphitic acid or benzenehexacarboxylic acid, is an acid first discovered in 1799 by Martin Heinrich Klaproth in the mineral mellite (honeystone), which is the aluminium salt of the acid. It crystallizes in fine silky needles and is soluble in water and alcohol. Preparation Mellitic acid may be prepared by warming mellite with ammonium carbonate, boiling off the excess of the ammonium salt, and adding ammonia to the solution. The precipitated alumina is filtered off, the filtrate evaporated, and the ammonium salt of the acid purified by recrystallization. The ammonium salt is then converted into the lead salt by precipitation with lead acetate, and the lead salt is then decomposed by hydrogen sulfide. The acid may also be prepared by the oxidation of pure carbon, graphite or hexamethylbenzene, by alkaline potassium permanganate in the cold, or by hot concentrated nitric acid. Reactions It is a very stable compound; chlorine, concentrated nitric aci ...
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Dimethylacetylene
2-Butyne (dimethylacetylene, crotonylene or but-2-yne) is an alkyne with chemical formula CH3C≡CCH3. Produced artificially, it is a colorless, volatile, pungent liquid at standard temperature and pressure. 2-Butyne is of interest to physical chemists because of its very low torsional barrier and the problem of determining that barrier using high-resolution infrared spectroscopy. Analysis of its spectrum leads to a determination that the torsional barrier is only 6 cm−1 (1.2 J or 72 J mol−1). However, it has not been determined whether the equilibrium structure is eclipsed (D3h) or staggered (D3d). Symmetry analysis using the Molecular Symmetry Group G36 shows that one would need to analyse its high resolution rotation-vibration Raman spectrum to determine its equilibrium structure. 2-Butyne (''dimethylethyne'') forms with 5-decyne (''dibutylethyne''), 4-octyne (''dipropylethyne'') and 3-hexyne (''diethylethyne'') a group of symmetric alkynes. Synthesis 2-Butyne can ...
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Alkyne Trimerisation
In organic chemistry, an alkyne trimerisation is a +2+2nbsp; cycloaddition reaction in which three alkyne units () react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applicable to organic synthesis. Being a cycloaddition reaction, it has high atom economy. Many variations have been developed, including cyclisation of mixtures of alkynes and alkenes as well as alkynes and nitriles. Mechanism and stereochemistry Trimerisation of acetylene to benzene is highly exergonic, proceeding with a free energy change of 142 kcal/mol at room temperature. Kinetic barriers however prevent the reaction from proceeding smoothly. The breakthrough came in 1948, when Reppe and Schweckendiek reported their wartime results showing that nickel compounds are effective catalysts: : 3 RC2H -> C6R3H3 Since this discovery, many other cyclotrimerisations have been reported. Mechanism In terms of mechanism, the reactions beg ...
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Reaction Intermediate
In chemistry, a reaction intermediate or an intermediate is a molecular entity that is formed from the reactants (or preceding intermediates) but is consumed in further reactions in stepwise chemical reactions that contain multiple elementary steps. Intermediates are the reaction product of one elementary step, but do not appear in the chemical equation for an overall chemical equation. For example, consider this hypothetical stepwise reaction: :A + B -> C + D The reaction includes two elementary steps: :A + B -> X :X -> C + D In this example, X is a reaction intermediate. IUPAC definition The IUPAC Gold Book defines an ''intermediate'' as a compound that has a lifetime greater than a molecular vibration that is formed (directly or indirectly) from the reactants and reacts further to give (either directly or indirectly) the products of a chemical reaction. The lifetime condition distinguishes true, chemically distinct intermediates from vibrational states or such transition st ...
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